CA2738164A1 - Procedes de fabrication d'acide adipique a partir de bouillons de fermentation contenant de l'adipate de diammonium - Google Patents

Procedes de fabrication d'acide adipique a partir de bouillons de fermentation contenant de l'adipate de diammonium Download PDF

Info

Publication number: CA2738164A1
Authority: CA; Canada
Prior art keywords: broth; bottoms; water; liquid; seq
Prior art date: 2010-04-30
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Granted

Application number

CA2738164A

Other languages

English (en)

Other versions

CA2738164C (fr

Inventor

Olan S. Fruchey

Leo E. Manzer

Dilum Dunuwila

Brian T. Keen

Brooke A. Albin

Nye A. Clinton

Bernard D. Dombek

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bioamber Inc

Original Assignee

Bioamber SAS

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2010-04-30

Filing date

2011-04-21

Publication date

2011-10-30

2011-04-21 Application filed by Bioamber SAS filed Critical Bioamber SAS

2011-10-30 Publication of CA2738164A1 publication Critical patent/CA2738164A1/fr

2014-03-25 Application granted granted Critical

2014-03-25 Publication of CA2738164C publication Critical patent/CA2738164C/fr

Status Expired - Fee Related legal-status Critical Current

2031-04-21 Anticipated expiration legal-status Critical

Links

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230000004151 fermentation Effects 0.000 title claims abstract description 55
238000000034 method Methods 0.000 title claims abstract description 51
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 title description 184
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235000011037 adipic acid Nutrition 0.000 title description 92
235000010633 broth Nutrition 0.000 title description 66
ZRSKSQHEOZFGLJ-UHFFFAOYSA-N ammonium adipate Chemical compound [NH4+].[NH4+].[O-]C(=O)CCCCC([O-])=O ZRSKSQHEOZFGLJ-UHFFFAOYSA-N 0.000 title description 32
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HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
238000011118 depth filtration Methods 0.000 description 1
238000013461 design Methods 0.000 description 1
150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 1
150000001991 dicarboxylic acids Chemical class 0.000 description 1
235000015872 dietary supplement Nutrition 0.000 description 1
ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
229910000396 dipotassium phosphate Inorganic materials 0.000 description 1
235000019797 dipotassium phosphate Nutrition 0.000 description 1
229940032049 enterococcus faecalis Drugs 0.000 description 1
239000010408 film Substances 0.000 description 1
229940044170 formate Drugs 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
239000008103 glucose Substances 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
150000002484 inorganic compounds Chemical class 0.000 description 1
229910010272 inorganic material Inorganic materials 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical class CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
WRUGWIBCXHJTDG-UHFFFAOYSA-L magnesium sulfate heptahydrate Chemical compound O.O.O.O.O.O.O.[Mg+2].[O-]S([O-])(=O)=O WRUGWIBCXHJTDG-UHFFFAOYSA-L 0.000 description 1
239000012092 media component Substances 0.000 description 1
230000008018 melting Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
235000019796 monopotassium phosphate Nutrition 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
239000003921 oil Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
238000010935 polish filtration Methods 0.000 description 1
229920006393 polyether sulfone Polymers 0.000 description 1
GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
238000011085 pressure filtration Methods 0.000 description 1
JXOHGGNKMLTUBP-HSUXUTPPSA-N shikimic acid Chemical compound O[C@@H]1CC(C(O)=O)=C[C@@H](O)[C@H]1O JXOHGGNKMLTUBP-HSUXUTPPSA-N 0.000 description 1
JXOHGGNKMLTUBP-JKUQZMGJSA-N shikimic acid Natural products O[C@@H]1CC(C(O)=O)=C[C@H](O)[C@@H]1O JXOHGGNKMLTUBP-JKUQZMGJSA-N 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000012265 solid product Substances 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
239000010409 thin film Substances 0.000 description 1
238000007738 vacuum evaporation Methods 0.000 description 1
238000009834 vaporization Methods 0.000 description 1
230000008016 vaporization Effects 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1
239000011782 vitamin Substances 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
229930003231 vitamin Natural products 0.000 description 1
239000012138 yeast extract Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/02—Preparation of carboxylic acids or their salts, halides or anhydrides from salts of carboxylic acids
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/34—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping with one or more auxiliary substances
- B01D3/36—Azeotropic distillation
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
- C07C51/44—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation by distillation
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
- C07C51/44—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation by distillation
- C07C51/46—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation by distillation by azeotropic distillation
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C55/00—Saturated compounds having more than one carboxyl group bound to acyclic carbon atoms
- C07C55/02—Dicarboxylic acids
- C07C55/14—Adipic acid
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/40—Preparation of oxygen-containing organic compounds containing a carboxyl group including Peroxycarboxylic acids
- C12P7/44—Polycarboxylic acids
- C12P7/46—Dicarboxylic acids having four or less carbon atoms, e.g. fumaric acid, maleic acid

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Oil, Petroleum & Natural Gas (AREA)
Wood Science & Technology (AREA)
Life Sciences & Earth Sciences (AREA)
Zoology (AREA)
Crystallography & Structural Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Microbiology (AREA)
Biotechnology (AREA)
Health & Medical Sciences (AREA)
Biochemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
General Engineering & Computer Science (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)

CA2738164A 2010-04-30 2011-04-21 Procedes de fabrication d'acide adipique a partir de bouillons de fermentation contenant de l'adipate de diammonium Expired - Fee Related CA2738164C (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US32980010P	2010-04-30	2010-04-30
US61/329,800		2010-04-30
US13/087,001		2011-04-11
US13/087,001 US20110269993A1 (en)	2010-04-30	2011-04-14	Processes for producing adipic acid from fermentation broths containing diammonium adipate

Publications (2)

Publication Number	Publication Date
CA2738164A1 true CA2738164A1 (fr)	2011-10-30
CA2738164C CA2738164C (fr)	2014-03-25

Family

ID=44247841

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA2738164A Expired - Fee Related CA2738164C (fr)	2010-04-30	2011-04-21	Procedes de fabrication d'acide adipique a partir de bouillons de fermentation contenant de l'adipate de diammonium

Country Status (8)

Country	Link
US (1)	US20110269993A1 (fr)
EP (1)	EP2383249A1 (fr)
JP (1)	JP2013524833A (fr)
KR (1)	KR20130037680A (fr)
CN (1)	CN103282337A (fr)
BR (1)	BRPI1101896A2 (fr)
CA (1)	CA2738164C (fr)
WO (1)	WO2011136942A1 (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2011119427A1 (fr)	2010-03-26	2011-09-29	Bioamber S.A.S.	Procédés de production de monosuccinate d'ammonium à partir de bouillons de fermentation contenant un disuccinate d'ammonium, un monosuccinate d'ammonium et/ou de l'acide succinique, et conversion du monosuccinate d'ammonium en acide succinique
US20120021473A1 (en) *	2010-04-01	2012-01-26	Bioamber S.A.S.	Processes for producing carboxylic acids from fermentation broths containing their ammonium salts
BR112012031877A2 (pt) *	2010-06-16	2015-09-22	Bioamber Sas	processo para produzir caprolactam e derivados do mesmo de caldos de fermentação contendo adipato de diamônio ou adipato de monomônio.
CA2949869C (fr) *	2014-06-10	2023-11-28	Bioamber Inc.	Acides organiques issus de l'homocitrate et de derives d'homocitrate

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3433830A (en) *	1964-09-30	1969-03-18	Chevron Res	Aliphatic dicarboxylic acid purification process
JPS5543759B2 (fr) *	1972-06-28	1980-11-07
DE2718363A1 (de) *	1977-04-25	1978-10-26	Roehm Gmbh	Verfahren zur herstellung von carbonsaeuren aus ihren ammoniumsalzen
US4480034A (en) *	1982-06-10	1984-10-30	Celanese Corporation	Continuous fermentation process and bioconversion-product recovery
US5034105A (en) *	1989-07-27	1991-07-23	Michigan Biotechnology Institute	Carboxylic acid purification and crystallization process
US5487987A (en) *	1993-09-16	1996-01-30	Purdue Research Foundation	Synthesis of adipic acid from biomass-derived carbon sources
WO1999000350A1 (fr) *	1997-06-26	1999-01-07	Nippon Soda Co., Ltd.	Procede de production d'acides libres a partir de carboxylates d'ammonium
US6498242B1 (en)	1999-02-19	2002-12-24	E. I. Du Pont De Nemours And Company	Biological method for the production of adipic acid and intermediates
JP4061426B2 (ja) *	2002-05-10	2008-03-19	三菱化学株式会社	有機酸の製造方法
JP4831394B2 (ja) *	2003-10-09	2011-12-07	独立行政法人産業技術総合研究所	カルボン酸系化合物の製造方法
EP1632568A1 (fr) *	2004-09-03	2006-03-08	Nederlandse Organisatie voor toegepast-natuurwetenschappelijk Onderzoek TNO	Procédé et dispositif pour la production et séparation des produits de fermentation
JP5365824B2 (ja) *	2006-03-23	2013-12-11	独立行政法人産業技術総合研究所	コハク酸ジアルキルの製造方法および１，４−ブタンジオールの製造方法
SI2265709T1 (en)	2008-03-27	2018-03-30	Genomatica, Inc.	MICROORGANISMS FOR PREPARATION OF ADYPIC ACID AND OTHER COMPOUNDS
CN107267562A (zh)	2008-07-08	2017-10-20	帝斯曼知识产权资产管理有限公司	通过在低pH下发酵生产二羧酸
CN102858731A (zh) *	2010-04-01	2013-01-02	生物琥珀酸有限公司	用于从含有琥珀酸二铵的发酵液制备琥珀酸的方法
KR20130020779A (ko) *	2010-04-01	2013-02-28	바이오엠버 인터내셔널 에스.에이.알.엘.	숙신산염으로부터 테트라하이드로퓨란, 감마-부티로락톤 및/또는 부탄디올의 제조방법
EP2571838A1 (fr) *	2010-04-30	2013-03-27	Bioamber, S.A.S.	Procédés de fabrication d'acides composés hooc-r-cooh à partir de bouillons de fermentation contenant des composés nh4+ -ooc-r-coo-nh4+

2011
- 2011-04-14 US US13/087,001 patent/US20110269993A1/en not_active Abandoned
- 2011-04-15 JP JP2013508005A patent/JP2013524833A/ja active Pending
- 2011-04-15 WO PCT/US2011/032617 patent/WO2011136942A1/fr not_active Ceased
- 2011-04-15 CN CN2011800320625A patent/CN103282337A/zh active Pending
- 2011-04-15 KR KR1020127030812A patent/KR20130037680A/ko not_active Ceased
- 2011-04-21 CA CA2738164A patent/CA2738164C/fr not_active Expired - Fee Related
- 2011-04-29 BR BRPI1101896-8A patent/BRPI1101896A2/pt not_active Application Discontinuation
- 2011-05-02 EP EP11164481A patent/EP2383249A1/fr not_active Withdrawn

Also Published As

Publication number	Publication date
EP2383249A1 (fr)	2011-11-02
JP2013524833A (ja)	2013-06-20
KR20130037680A (ko)	2013-04-16
BRPI1101896A2 (pt)	2012-10-02
CA2738164C (fr)	2014-03-25
CN103282337A (zh)	2013-09-04
US20110269993A1 (en)	2011-11-03
WO2011136942A1 (fr)	2011-11-03

Publication	Publication Date	Title
CA2738166C (fr)	2013-12-24	Procedes de fabrication d'adipate d'ammonium a partir de bouillons de fermentation contenant de l'adipate de diammonium, de l'adipate de monoammonium et/ou d'acide adipique, et conversion de l'adipate de monoammonium en acide adipique
US8742060B2 (en)	2014-06-03	Processes for producing hexamethylenediamine (HMD), adiponitrile (ADN), adipamide (ADM) and derivatives thereof
CA2738164C (fr)	2014-03-25	Procedes de fabrication d'acide adipique a partir de bouillons de fermentation contenant de l'adipate de diammonium
US8703900B2 (en)	2014-04-22	Processes for producing caprolactam and derivatives thereof from fermentation broths containing diammonium adipate, monoammonium adipate and/or adipic acid
US20130158229A1 (en)	2013-06-20	Processes for the production of hydrogenated products and derivatives thereof
EP2582678B1 (fr)	2016-12-07	Procédés pour produire du caprolactame et des dérivés de celui-ci à partir de bouillons de fermentation contenant de l'adipate de diammonium ou de l'adipate de monoammonium
WO2012170060A1 (fr)	2012-12-13	Procédés de production d'hexanediol (hdo), d'hexaméthylènediamine (hmd) et de dérivés de ceux-ci
HK1162459A (en)	2012-08-31	Processes for producing adipic acid from fermentation broths containing diammonium adipate
CA2800708A1 (fr)	2011-12-22	Procedes de production d'hexamethylenediamine (hmd), d'adiponitrile (adn), d'adipamide (adm), et de leurs derives
US20130150551A1 (en)	2013-06-13	Processes for the production of hydrogenated products and derivatives thereof
WO2012170059A1 (fr)	2012-12-13	Procédés de production d'hexanediol (hdo) et d'hexaméthylènediamine (hmd) à partir de bouillons de fermentation contenant de l'acide adipique
HK1161871A (en)	2012-08-10	Processes for producing monoammonium adipate from fermentation broths containing diammonium adipate, monoammonium adipate and/or adipic acid, and conversion of monoammonium adipate to adipic acid
US20140228595A1 (en)	2014-08-14	Processes for producing hexanediol (hdo), hexamethylenediamine (hmd), adiponitrile (adn), adipamide (adm) and derivatives thereof
HK1180329A (en)	2013-10-18	Processes for producing caprolactam and derivatives thereof from fermentation broths containing diammonium adipate or monoammonium adipate

Legal Events

Date	Code	Title	Description
2011-06-23	EEER	Examination request
2022-12-03	MKLA	Lapsed	Effective date: 20210421